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Photo by Kevin Deems.

“The price of being a sheep is boredom. The price of being a wolf is loneliness. Choose one or the other with great care.” —Hugh McCleod

Several close friends of mine are talking about getting out of jobs they are unhappy with and getting closer to the life they imagined. I am also asked daily by students at the shows we play at high schools, “How can I make it as a singer, writer, musician, creative, etc.?”

Well, here is a short rant, as well as my five favorite books on the subject.

It takes an unbelievable amount of time and risk to be an entrepreneur, as you would expect. “Nothing ventured, nothing gained” sounds like fortune-cookie wisdom, but it’s dead on.

I have been extremely fortunate to have not had a day job for more years than I can remember, but it came at the price of little sleep, my family not hearing from me as much as they should, and time with my loved ones being interrupted by a phone call so I could be available to people trying to help me achieve my dream. Selfish to always be on your phone? Yes, and I hate it. But when YOU ARE YOUR OWN BOSS and you aren’t answering, there’s a good chance you won’t be eating at some point soon. And If I’m not answering as the one with my name on the marquee, then that means the crew I represent and pay aren’t eating, either. If you aren’t 100 percent passionate and committed to what you are trying to achieve, you can’t expect those working with you to rise to the occasion.

If you want to step out on your own and bet it all, you have to be ready for some major change in your life. If you want out of your nine to five, get ready to work six to 12. That’s 6:00 a.m. to 12:00 p.m. Now, this is where those of you who are sane talk to me about balance and not burning out, and you are of course right. There is no point in “gaining the world and losing your soul”—i.e., making money or getting famous or successful at the cost of your relationships. But I can’t overstate enough, especially to young people who ask me about this life, that to do it successfully—to live on the road and chase your dreams—there are trade-offs, and there is a price you gotta pay. The grass is always greener – Everyone I know in a day job wants to travel and explore more, and those of us on the road most of the year would kill for a comfy bed, cooked food, and a better insurance plan.

Lastly, it’s important to go in knowing what success means to you and not what we see on TV or on our Instagram feeds. If you want balance with family, then maybe keeping the day job and working off hours at your art is perfect for you. (Most people who live on the road, at least in the early years, for better or worse, have no attachments back home.) If you don’t LOVE it, then you won’t be in it for the long haul ’cause those around entrepreneurs are usually in for a wild ride. The flip side of excitement and risk is, of course, instability and chaos, and most artists bring that with ’em in droves. We need to mitigate that chaos, not wear it as a badge of honor. I fully believe you can work at conquering your demons and still be creative, otherwise I would of burnt out long ago.

Here are the five best (and quickest) books I have read on how to become YOURSELF. How to shake off fear and go at your dreams. How to get out of the “rat race” and take a hold of a little bigger life. I’m always interested in reading about conquering fear, putting in the hours, making luck by showing up. I am a geek for all self-help and bios. These books got me in the mindset to do my own work my own way, and I hope they help you half as much as they helped me.

1. The War of Art, Steven Pressfield. One of the heaviest books ever. If there is anything in your life you can’t break through, his definition and examinations of “resistance” will floor you. Plus it keeps the focus on DOING THE WORK – not the marketing and 1000 other things musicians are expected to do these days. Without the work none of that marketing is gonna matter anyway. Thanks to Erin O’ Neill for this little miracle of a book.

2. Ignore Everybody, Hugh McCleod. Thanks to Wade Hampton for this piece of fire. I could take the first line of any chapter and sit it right here and it would feel like a manifesto that you could discuss over a whiskey for an hour. The quote that kicked this blog off is a perfect example.

3. Anything You Want, Derek Sivers. You can read this in like an hour or two. This book gave me permission to stop trying to do everything myself. “Whatever you don’t like to do, someone else does.” It’s also interesting that cat set up a trust FOR HIMSELF WHILE HE IS ALIVE so he wouldn’t blow all the money he was making but made sure he was giving it to charity. Awesome.

4. Linchpin, Seth Godin. Become who you are. Give value. Think outside the box. Don’t worry about the ladder of success ’cause it’s old hat. Make yourself valuable to others and treat others right, and there will always be work to do. I love how he says, “Artist’s ship,” meaning nothing is perfect. You have to do the work; you have to finish and get it out the door. Take away some of the mystery and magic and just get it done, be dependable, learn from mistakes, etc.

5. The Art of Asking, Amanda Palmer. This one is a little more inside ball, but if you are someone who has had fear moving into the social media world in general, this will get you fired up. The ending is also stunningly beautiful. Amanda is the pioneer musician frontwoman who had the first million-dollar Kickstarter.

Would love to hear about the books that have moved you!

Up soon—some of my fave podcasts. Thanks for joining me, and see you next Wednesday!


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Photo by Kevin Deems.

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